HRID2418588

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CSCC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](N)Cc1ccccc1)C(N)=O.Cl

HCID131713768

未命名化合物

结构：CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O.NNC(=O)[C@@H](N)Cc1ccccc1.O=C(O)c1cc(Br)c(Br)[nH]1

HCID131713773

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)O.CSCC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@@H](N)Cc1ccccc1)C(N)=O.O=C(O)c1cc(Br)c(Br)[nH]1

HCID131713771

未命名化合物

收率 51%

PROCEDURE

实验过程

Condensation of each of BocPro-LBpa-PheNHNH2 (1.20 g.) and BocPro-DBpa-PheNHNH2 (0.450 g.) with HDPhe-Leu-MetNH2 hydrochloride salt (Example 23, 1.02 g., 0.445 g.) by the acyl azide method (Yajima et al., Chem. Pharm. Bull., vol. 19, p. 1900, 1971) gave BocPro-LBpa-Phe-DPhe-Leu-MetNH2 in 51% yield and BocPro-DBpa-Phe-DPhe-Leu-MetNH2 in 44% yield. De-t-butoxycarbonylation of BocPro-LBpa-Phe-DPhe-Leu-MetNH2 (0.500 g.) and BocPro-DBpa-Phe-DPhe-Leu-MetNH2 (0.250 g.) using hydrogen chloride in dioxane gave HPro-LBpa-Phe-DPhe-Leu-MetHN2, which was isolated as the amorphous white solid dihydrochloride salt hydrate (2:9) in 53% yield, and HPro-DBpa-Phe-DPhe-Leu-MetNH2, which was isolated as the dihydrochloride salt hexahydrate in 59% yield.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4b17b090cf3148b68a2a28ac5d29f05a
来源数据集: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04472305
来源说明: uspto-grants-1984_09

反应 SMILES

[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[CH:16]1[C:20]([Br:21])=[C:19]([Br:22])[NH:18][C:17]=1[C:23]([OH:25])=[O:24].[NH2:26][C@H:27]([C:35]([NH:37]N)=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N[C@@H:40]([C:48]([NH:50][C@H:51]([C:56]([NH:58][C@H:59]([C:64]([NH2:66])=[O:65])[CH2:60][CH2:61][S:62][CH3:63])=[O:57])[CH2:52][CH:53]([CH3:55])[CH3:54])=[O:49])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.Cl>>[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[CH:16]1[C:20]([Br:21])=[C:19]([Br:22])[NH:18][C:17]=1[C:23]([OH:25])=[O:24].[NH2:26][C@H:27]([C:35]([NH:37][C@@H:40]([C:48]([NH:50][C@H:51]([C:56]([NH:58][C@H:59]([C:64]([NH2:66])=[O:65])[CH2:60][CH2:61][S:62][CH3:63])=[O:57])[CH2:52][CH:53]([CH3:54])[CH3:55])=[O:49])[CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1